The closely watched trial of prominent attorney Tom Goldstein officially began this week, and it’s already shaping up to blend the worlds of law, poker, and Hollywood. Goldstein, who is facing federal charges related to alleged tax fraud tied to high-stakes poker winnings, could see testimony from several high-profile figures—among them, actor Tobey Maguire.
Prosecutors say Maguire may be called as a witness in connection with a dispute over a massive poker debt, one that reportedly totaled around $15 million and traces back to elite, private poker games.
Alleged Poker Debt at the Center of the Case
According to court statements cited by Reuters, Goldstein once represented Maguire in an effort to recover millions the actor allegedly won during a 2019 poker game against a Texas billionaire. Prosecutors told jurors that Maguire paid Goldstein a $500,000 legal fee for his services—but claim that the money was ultimately routed to someone Goldstein personally owed from his own poker losses.
The original indictment, first reported in early 2025, referenced a “Hollywood actor” who had not been paid out approximately $15.6 million in poker winnings. That actor is now widely understood to be Maguire. Prosecutors allege that Goldstein transferred Maguire’s legal fee to a third party—later identified as California real estate developer Bob Safai—to reduce a poker debt Goldstein himself owed, reportedly totaling around $14 million.
Maguire is not accused of any wrongdoing in the case.
Maguire’s Longstanding Poker Connections
While Maguire has largely avoided the public poker spotlight in recent years, his history in the game is well documented. He was famously revealed as the mysterious “Player X” in Molly’s Game and was later linked to high-stakes home games involving celebrities and ultra-wealthy businessmen. He was also named in a civil lawsuit after reportedly winning large sums from convicted fraudster Brad Ruderman, whose investors later sought to recover losses.
In the early 2000s, Maguire was a regular presence at the World Series of Poker, though he has since stepped away from tournament play. Still, he occasionally resurfaces in private games, most recently appearing at a poker night during Timothée Chalamet’s Oscar party in February 2025.
Opening Week Brings Billionaire Testimony
The first week of Goldstein’s trial included jury selection, opening statements, and testimony from billionaire Alec Gores. Gores, a government witness, reportedly claimed he lost more than $26 million to Goldstein in heads-up poker matches. Prosecutors suggested Gores also suffered heavy losses to Dan Bilzerian, a close associate of Goldstein.
Goldstein’s defense attorney, Stephany Reaves Couper, pushed back strongly in her opening remarks, arguing that prosecutors have mischaracterized the facts. She described Goldstein as a lawyer acting in good faith while juggling a demanding legal career, including arguing cases before the U.S. Supreme Court.
Prosecutors, however, painted a very different picture. They allege Goldstein failed to report millions of dollars in poker winnings dating back to 2016, claiming the money financed what they described as an increasingly extravagant lifestyle.
“This case is about Mr. Goldstein’s choices and his deception,” prosecutor Hayter Whitman told jurors.
Charges Narrowed, Trial Continues
Goldstein was originally charged with 22 counts, though that number has since been reduced to 16. He has pleaded not guilty to all charges and has reportedly declined two plea deals offered by prosecutors.
As the trial moves forward, the potential appearance of Tobey Maguire could bring even more attention to a case that already sits at the crossroads of celebrity culture, underground poker, and federal tax law.
